Ethyl Acetate → 5-Vinylnicotinonitrile

HRID 606827

반응식

HRID 606827 반응식
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23])=[CH2:2]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 81998TributylvinyltinHCID 7367935-Bromonicotinonitrile

생성물 1

HCID 670475755-Vinylnicotinonitrile수율 70.3%

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

Add bis(triphenylphosphine)palladium (II) dichloride (0.460 g, 0.66 mmol) and tributyl-vinyl-stannane (7.2 mL, 24.6 mmol) to a solution of 5-bromonicotinonitrile (3.0 g, 16.4 mmol) in toluene (50 mL) and stir at 110° C. for 150 min. Add an aqueous saturated solution of ammonium chloride and ethyl acetate and separate the layers. Wash the organic layer twice with an aqueous saturated solution of potassium fluoride and once with water. Dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 3:1 hexane:ethyl acetate, to give the title compound (1.5 g, 70%).

후처리

  1. customseparate the layers
  2. washWash the organic layer twice with an aqueous saturated solution of potassium fluoride
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 3:1 hexane

출처 및 근거

ORD 기록
ord-56b43414d3494c388f5d80d9389fb119
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

연결된 노트

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